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It took me 26 years to find a pair of pants I really, truly liked: a pair of slim black jeans. Problem was, by the time I was just getting comfortable in the new me, baggy was back in, jeans were back out, and I'd blown the crotch out of my precious A.P.C.'s—twice.

Finding replacement bottoms should have been easy. There's never been a better time, I was assured, to be a pants haver. But for someone new to the trousers game, the breadth of choice was paralyzing.

On a trip to Barneys, everything I pulled off the racks was compelling: the joyously spacious drop-crotch AMIs; a pair of blue slacks with white piping from Officine Générale; single-pleated wide-leg Dries Van Notens that made me feel—and look—like the coolest Newsie in all of New York (and, their costing half a grand, probably the richest in the history of newsboys).

I liked all of them, but in a way that felt more about novelty than authenticity. So I called up Josh Peskowitz, co-owner of L.A.'s Magasin and the type of pants whisperer I needed. He said I could experiment with pattern or color or shape—but definitely not all three. So I went to Todd Snyder in Midtown Manhattan, where I immediately fell for a cotton pair that reminded me of the Dries bottoms but were not quite as billowy (and so significantly less Depression-era). Also, they were light green—neutral enough but different from anything I owned. They fit perfectly in the sweet spot between casual and formal that, increasingly, is my daily uniform. They'd go from fashion-magazine job to oddly sticky dive bar seamlessly. Most important: They felt like they were on my wavelength—which brought me back to something Peskowitz had said.

If you wear things that make you happy, “you're exuding a level of confidence that will help you carry those items of clothing, even if they're a little outside of your pre-described comfort zone.” Reader, I bought them. And I still look forward to blowing out the crotch.

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